Synthesis and properties of sym-pentasubstituted derivatives of corannulene.

Alkyl, aryl, and alkynyl as well as heteroatom derivatives of sym-pentasubstituted corannulenes have been synthesized from sym-pentachlorocorannulene. These units form potential building blocks for future work on superstructures based on corannulene. Absorption/emission properties follow expected trends from the parent 1. sym-Pentasubstitution gives rise to variations in the chemical dynamics of bowl inversion. van der Waals attraction is cited to explain an anomalously high barrier to bowl inversion in 10.